title: Asymmetric synthesis of α-chloro-β-amino-N-sulfinyl imidates as chiral building blocks.
abstract: New chiral α-chloro-β-amino-N-sulfinyl imidates were synthesized in high yield and excellent diastereomeric excess via highly anti-selective Mannich-type reactions of (R(S))-methyl N-tert-butanesulfinyl-2-chloroethanimidate with aromatic aldimines. The α-chloro-β-amino-N-sulfinylimidates proved to be excellent building blocks for the asymmetric synthesis of β-amino-α-chloro amides and esters, aziridine-2-carboxylic amides and esters, trans-2-aryl-3-chloroazetidines, and methyl 4-phenyloxazolidin-2-one-5-carboxylate. The obtained absolute anti-diastereoselectivity is the opposite of the stereochemical outcome observed for α-methyl-substituted imidates.
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Filip
authors.initials: F
authors.lastname: Colpaert
authors.forename: Sven
authors.initials: S
authors.lastname: Mangelinckx
authors.forename: Stijn
authors.initials: S
authors.lastname: De Brabandere
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D007096:Imidoesters / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C561206:(R(S))-methyl N-tert-butanesulfinyl-2-chloroethanimidate; D007096:Imidoesters; D013452:Sulfonium Compounds